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Synthesis of 15-Cyano-12-oxopentadecano-15-lactone and 15-Cyano- 12-oxopentadecano-15-lactam

✍ Scribed by Peng Wu; Xiao-Mei Liang; Jian-Jun Zhang; Yue-Mei Jia; Yan-Hong Dong; Jia-Xing Huang; Fu-Heng Chen; Dao-Quan Wang

Publisher: John Wiley and Sons
Year: 2009
Tongue: German
Weight: 165 KB
Volume: 92
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.200900114

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✦ Synopsis

15-Cyano-12-oxopentadecano-15-lactone was synthesized in 59% total yield starting from 2nitrocyclododecanone by Michael addition to acrylaldehyde, followed by reaction with trimethylsilylcyanide, hydrolysis, ring-expansion, and Nef reaction. A two-step, one-pot synthesis of intermediate 2hydroxy-4-(1-nitro-2-oxycyclododecyl)butanenitrile from 3-(1-nitro-2-oxocyclododecyl)propanal was developed and the conditions for the Nef reaction were studied. 15-Cyano-12-oxopentadecano-15lactam was synthesized in 40% total yield starting from 2-nitrocyclododecanone by Michael addition to acrylaldehyde, followed by Strecker reaction, ring-expansion, and Nef reaction. The conditions for the Strecker and Nef reactions were studied. The structures of the target compounds, intermediates, and byproduct were characterized by IR, 1 H-and 13 C-NMR, and elemental analysis or MS.

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